Caligiuri is probably best remembered for his goal dubbed the "Shot Heard Round the World," which he scored in a World Cup Qualifier November 19, 1989 against Trinidad and Tobago, which qualified the United States for the 1990 FIFA World Cup in Italy, the first World Cup the United States had played in since 1950. Caligiuri was, however, far more than that single goal - he had a distinguished career, both for club teams and for the United States national team. On top of that, Caligiuri would go on to score the first World Cup goal for the national team in 40 years, scoring in a 5-1 defeat against Czechoslovakia.

After graduating from Walnut High School, Caligiuri attended UCLA from 1982 to 1985. He was named an NCAA All-American twice, the 1986 U.S. Soccer Athlete of the Year, and captained the Bruins to an NCAA Championship his junior year. While at UCLA Caligiuri also earned his first cap for the national team, playing October 9, 1984 against El Salvador. Caligiuri would eventually tally 110 appearances for the United States, and would add five goals from his position in the midfield. Caligiuri was a central figure to the national team throughout the 80's up to the mid-90's, and would start every match in both the 1990 and 1994 FIFA World Cups, playing his final game in 1997, thirteen years after his debut.

After graduating from UCLA, Caligiuri played for the San Diego Nomads of the Western Soccer Alliance for a single season in 1986. He was league MVP. He also played with the U.S. Futsal team, earning 4 caps and scoring a single goal this year.

After being named WSA MVP and the U.S. Player of the Year in 1986, he attracted the attention of German Bundesliga club Hamburger SV. He signed with the team after playing in the 1986 FIFA/UNICEF All Star Game. However, he never managed to break into the first team.

On March 14, 1990, he signed a contract with USSF making him a full time national team member.[1] He remained on contract with USSF for several years. In 1993, he briefly considered moving to a British or German club after he was left off the Gold Cup roster, but decided instead to re-dedicate himself to the national team in preperation for the 1994 World Cup. Following the World Cup, he returned to Germany to play for Second Bundesliga club SC Freiburg.

On May 4 1995, Caliguiri he returned to the U.S. from Germany to sign with the Los Angeles Salsa of the American Professional Soccer League. He decided to play for the Salsa as a way of gaining match fitness before the U.S. national team games that summer. He donated his entire salary from the Salsa to the victims of the Oklahoma City bombing.[2] In August, the Salsa loaned Caligiuri to Bundesliga club FC St. Pauli, appearing in 14 games. However, January 1996, the team elected not to exercise an option in Caligiuri's contract and allowed him to return to the U.S. When he did, he signed with the emerging Major League Soccer. Caligiuri negotiated a promise from the league to let him play for his hometown Los Angeles Galaxy, but MLS allocated him to the Columbus Crew. While he played one season with the Crew, he fought the allocation. After an extended lawsuit in the first season, Caligiuri was placed with Los Angeles for the 1997 season, and would play with them until his retirement in 2001. Caligiuri finished his MLS career with 9 goals and 14 assists, accumulated over 135 games, 123 of which were starts.

Caligiuri had no trouble finding a job after his retirement, and was appointed head coach of both the men and women's soccer teams at Cal Poly Pomona before the beginning of their 2001 fall season, although he did not take over until 2002.